2-噻吩醇 | 17236-58-7

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 2-噻吩醇
• 英文名称: thiophen-2-ol
• 英文别名: 2-hydroxythiophene；2-Hydroxy-thiophen；hydroxy-thiophene
• CAS: 17236-58-7
• 化学式: C₄H₄OS
• mdl: MFCD01075765
• 分子量: 100.141
• InChiKey: WZMPOCLULGAHJR-UHFFFAOYSA-N

物化性质

• 熔点：
  9°C
• 沸点：
  218°C
• 密度：
  1.2550
• 保留指数：
  956

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-噻吩醇 以 水 、 乙腈 为溶剂， 生成 2(5H)-噻吩酮
  参考文献：
  名称：

  五元氧、氮和硫杂环的单羟基衍生物的互变异构

  摘要：

  Cinetique de cetomisation de divers enols heterocycliques generices par hydrolyse de leurs 衍生出三甲基甲硅烷基。恒定不变的恒等式

  DOI：

  10.1021/ja00196a046
• 作为产物：
  描述：

  噻吩 在 hemicucurbit[6]uril 作用下， 以 重水 为溶剂， 生成 2-噻吩醇
  参考文献：
  名称：

  Hemicucurbit[6]uril-induced aerobic oxidation of heterocyclic compounds

  摘要：

  The aerobic oxidation of furan in aqueous solution in the presence of HemiQ[16] has been investigated, and the product furan-2,5-diol is stabilized by encapsulation of HemiQ[16], which could be transformed to the dione confirmation in acidic solution and escape from the macrocyclic compound. The H-1 NMR titration experiments of the host-guest interaction at different pH values suggest protonation should improve the encapsulation, and therefore an unique property that HemiQI6] can be protonated has been revealed. The oxidizing kinetics suggests that the procedure is a consecutive reaction with a series of constants k(1) =2.9 x 10(-2) min(-1) , k(2) = 2.7 x 10(-2) min(-1), and k(3) = 5.7 x 10(-3) min(-1), respectively. The kinetic investigation at pD =2.0 indicates the HemiQ[6]-catalytic oxidation of furan could be accelerated by acidification. As a consequence, a plausible mechanism has been established on the above evidences. 2-Methylfuran is employed to give the product 2-methylfuran-5-ol exhibiting a satisfied activity in this aerobic oxidation with the supramolecular catalysis of HemiQ[6], but the oxidation of thiophene is very slow in either neutral or acidic condition. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2013.08.025

文献信息

• Nickel‐Catalyzed Synthesis of <i>N</i> ‐(Hetero)aryl Carbamates from Cyanate Salts and Phenols Activated with Cyanuric Chloride
  作者：Iman Dindarloo Inaloo、Mohsen Esmaeilpour、Sahar Majnooni、Ali Reza Oveisi

  DOI：10.1002/cctc.202000876

  日期：2020.11.5

  one‐pot synthesis of N‐(hetero)aryl carbamates through the reaction between alcohols and in‐situ produced (hetero)aryl isocyanates in the presence of a nickel catalyst. The phenolic C−O bond was activated via the reaction of phenol with cyanuric chloride (2,4,6‐trichloro‐1,3,5‐triazine (TCT)) as an inexpensive and readily available reagent. This strategy provides practical access to N‐(hetero)aryl carbamates

  设计了一种简单有效的多米诺反应，并通过在镍催化剂存在下，醇与原位生成的（杂）芳基异氰酸酯之间的反应，单锅合成N-（杂）芳基氨基甲酸酯。通过苯酚与氰尿酰氯（2,4,6-三氯-1,3,5-三嗪（TCT））反应可以活化酚C-O键，这是一种廉价且易于获得的试剂。该策略提供了以高收率和高官能团相容性实际获得N-（杂）芳基氨基甲酸酯的方法。
• Nickel-catalyzed cyanation of phenol derivatives activated by 2,4,6-trichloro-1,3,5-triazine
  作者：Liang Wang、Yaoyao Wang、Jun Shen、Qun Chen、Ming-Yang He

  DOI：10.1039/c8ob01034j

  日期：——

  A nickel-catalyzed cyanation of phenol derivatives activated by 2,4,6-trichloro-1,3,5-triazine (TCT) using aminoacetonitrile as the cyanating agent is described. This catalytic system delivered the desired products in moderate to good yields with good substrate compatibility. The readily available starting materials, cost-effective nickel catalyst and metal-free cyanating agent are the major features

  描述了使用氨基乙腈作为氰化剂的被2,4,6-三氯-1,3,5-三嗪（TCT）活化的苯酚衍生物的镍催化氰化反应。该催化体系以中等至良好的产率提供了所需的产物，并具有良好的底物相容性。容易获得的原料，具有成本效益的镍催化剂和不含金属的氰化剂是本方法的主要特征。
• Novel CuCl2-cryptand-[2.2.Benzo] complex: A base free and oxidant free catalyst for Ipso-Hydroxylation of aryl/heteroaryl-boronic acids in water at room temperature
  作者：Sankar Jyoti Bora、Bolin Chetia

  DOI：10.1016/j.jorganchem.2017.09.011

  日期：2017.11

  A novel cryptand and its copper complex was synthesised, which found to have enormous catalytic activity towards ipso-hydroxylation of aryl or heteroarylboronic acids and esters in water without using H2O2 or other oxidising agent and base at room temperature. This newly developed method efficiently converts aryl boronic acids and esters as well as heteroaryl boronic acids to their corresponding phenols

  合成了一种新型的穴状体及其铜配合物，发现其在室温下对水中的芳基或杂芳基硼酸和酯的ipso-羟基化具有巨大的催化活性，而无需使用H 2 O 2或其他氧化剂和碱。这种新开发的方法可在很短的反应时间内以高收率高效地将芳基硼酸和酯以及杂芳基硼酸转化为相应的苯酚。已经发现该协议与各种各样的功能组完全匹配。该方法的优点是高收率，非常短的反应时间，易于分离，可重复使用至第6次。
• Chemoselective oxidation of aryl organoboron systems enabled by boronic acid-selective phase transfer
  作者：John J. Molloy、Thomas A. Clohessy、Craig Irving、Niall A. Anderson、Guy C. Lloyd-Jones、Allan J. B. Watson

  DOI：10.1039/c6sc04014d

  日期：——

  conventional protecting group strategies, enabling chemoselective oxidation of BMIDA species over normally more reactive BPin substrates. We also demonstrate the selective oxidation of diboronic acid systems with chemoselectivity predictable a priori. The utility of this method is exemplified through the development of a chemoselective oxidative nucleophile coupling.

  我们报道了含有两个可氧化硼基团的芳基有机硼系统的直接化学选择性布朗型氧化。碱性双相反应条件能够在硼酸频哪醇 (BPin) 酯存在下选择性形成硼酸三羟基硼酸酯并进行相转移，同时避免形态平衡。光谱研究验证了有机硼物质的碱促进相选择性辨别。这种现象在多种有机硼化合物中普遍存在，也可用于反转传统的保护基策略，使 BMIDA 物质能够在通常更具反应性的 BPin 底物上进行化学选择性氧化。我们还证明了二硼酸系统的选择性氧化具有可先验预测的化学选择性。该方法的实用性通过化学选择性氧化亲核试剂偶联的开发来例证。
• An efficient base and H₂O₂ free protocol for the synthesis of phenols in water and oxygen using spinel CuFe₂O₄ magnetic nanoparticles
  作者：Rituparna Chutia、Bolin Chetia

  DOI：10.1080/00958972.2020.1802437

  日期：2020.7.2

  Abstract An efficient base and H2O2 free protocol was used for the synthesis of phenols from boronic acids using biogenic CuFe2O4 magnetic nanoparticles as catalyst at room temperature in water and oxygen. The catalyst was prepared using the flowers of Lantana camara. The size of the nanoparticles was 4.27 nm. Base free and ligand free protocol, less time, excellent yields, room temperature, biogenic

  摘要 使用生物源性 CuFe2O4 磁性纳米粒子作为催化剂，在室温下在水和氧气中，使用一种有效的无碱和 H2O2 协议从硼酸合成酚。催化剂是用马缨丹花制备的。纳米颗粒的尺寸为 4.27 nm。无碱和无配体协议、时间短、产率高、室温、催化剂的生物合成、使用 O2 作为环境友好型氧化剂是本协议的优点。催化剂的可回收性为 5 个循环，磁性或催化活性没有损失。